Et₂Zn-Mediated Rearrangement of Bromohydrins

Lezhen Li, Peijie Cai, Qingxiang Guo and Song Xue*

*Department of Applied Chemistry, Tianjin University of Technology, Tianjin, 300191, China, and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China, Email: xuesongustc.edu.cn

L. Li, P. Cai, Q. Guo, S. Xue, J. Org. Chem., 2008, 73, 3452-3459.

DOI: 10.1021/jo800231s (free Supporting Information)

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Abstract

Reaction of β-bromo alcohols with 0.6 equiv of Et₂Zn forms a zinc complex in CH₂Cl₂ at room temperature, followed by 1,2-migration to give the corresponding carbonyl compounds. This mild and clean rearrangement is general for acyclic and cyclic bromohydrins, and a variety of ring-expansive and -contractive carbonyl compounds were obtained in very good yields.

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Key Words

α-Arylation, Bromohydrins

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ID: J42-Y2008-1180